What To Wear On A First Date (15 Ideas For Women)

You’ve finally found some time to pencil in a hot date with the cute guy you’ve been chatting with for a few weeks. You’re stoked, your friends are stoked, and your mom is especially stoked. Even if you’ve been on a million other dates, deciding what to wear on a first date is always a major dilemma.

But try not to panic.

Every girl on the face of the earth knows what you’re going through, and we’ve got you covered.

Today, we’ll discuss 15 worthy outfits that will not only help you feel confident on your first date but are also sure to land you a second one.

So, without further ado, let’s jump right in!

Classic Cutie Pie

Regardless of the date, it’s tough to go wrong with a classic look. If you’re heading out for bowling, mini-golf, or even a movie, high-waisted skinnies and vintage tee will fit the bill perfectly. Tuck your tee in and add your favorite leather belt.

You can pair this look with any shoe, but you can easily spice things up by tossing on a pair of black heels. This outfit looks great on anyone. Not only will it leave you with plenty of confidence, but your date will definitely be swooning.

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Dressed-Up Dining

If you’re anything like me, dinner dates can be a bit nerve-wracking—especially when you don’t know your date too well. But, on the upside, dressing up for a fancy dinner is always fun.

If you’re on the fence about what to wear to a nice restaurant, toss on your favorite cocktail dress and pair it with some classic stilettos. Or, for a simpler look, try a pair of black skinny jeans, a silk blouse, and a nice blazer.

Either option is a timeless look that will never go out of style.

Happy Hour Hotness

Are you heading to grab drinks after a long day at the office? No worries. You can rock that business look on your date as well.

If your office requires a professional dress, it’s simple to cross the look over into an evening affair. A nice choice is to go with a black pencil skirt and a tucked-in button-up blouse—a subtle plaid is a fun option.

If you’d like, swap out your blazer for a coy cardigan or a leather jacket, and bring along a pair of spunky heels.

Cocktail Queen

A cocktail date can be a fun, easy way to chat and get to know each other. It’s quick, to the point, and you aren’t obligated to stay long if you realize your date is a dud.

A knee-length wrap dress provides the perfect in-between vibe to help you feel comfortable yet still feel cute and flirty. Pair it with some strappy heels or sandals, and grab a matching bag.

If you’re not the dress type, jeans are equally as fitting alongside a nicer top.

Lunch-Date Love

Everyone loves lunch. It’s effortless and an excellent opportunity to look cute and still be casual. Now is the perfect time to toss on that knee-length, button-up shirt dress. You can wear it with some cute sandals, or pair it with some white sneakers.

Or, go more casual with a pair of white cropped jeans and a denim jacket layered above a simple tee. Add in some suede flats, and you’re good to go!

Chic Sugar Plum

If you’re on the hunt for a great chic look, look no further. A classy combo is the best way to exude confidence.

Slip into some white or black high-waisted trousers and pair them with a coordinating tank. Add in some accessories, including some pumps and a classic handbag.

On the sweetheart side, try a pleated midi skirt alongside a silk blouse. Wear it with some strappy sandals.

Groovy Gal

Take your date back in time with a little bit of retro flair; it’s currently all the rage in the fashion world.

If you’re into it, you can’t go wrong with some high-waisted denim flares to accentuate your best features. Add a cute statement top, some platform sneakers or heels, and dance the night away.

Revolutionized Romance

Calling all hopeless romantics: we’ve got the ideal date-night look for you. Perfect for a sunset picnic or a walk along the beach. Everyone looks beautiful in their best flowy floral midi dress.

Wear it with a simple eye makeup look and a classic red lip to make everything pop. My go-to shoe for the romantic vibe is a white sneaker, but strappy sandals will always fit the part.

Summer Soulmate

If you live in a warmer climate or it’s summer, dust off your best sundress, sister. A sundress is a beautiful choice for a date; it keeps things casual, but you’ll be sure to impress.

Find a pretty pattern to match with some sneakers, or toss on some comfortable sandals.

If you’re short on sundresses, try a pair of statement shorts with a fitted, square-neck tee–a super cute look to keep things fun and flirty.

Extra Eye Candy

Since when did looking a bit “extra” ever hurt anybody? That’s right, never. For those daring ladies, you can easily catch and hold your date’s attention with some bold patterns. But, be careful to execute your ensemble properly.

Try animal print or colorful block patterns to ease into the look. A leopard skirt is a classic go-to that is enticing but never overdone. Wear it with some black booties and a silk cami. Bring along a leather jacket or suede blazer in case you get chilly.

Casual Cardigan

A sweet cardigan is a stellar choice for a date in the park or a chill afternoon walk. Opt for something well-fitted and button her up.

Complement the sweater with a silk scarf—either around your neck or tied in your hair—and some vintage Levi jeans.

A classic pair of white sneakers or charming yet comfortable heels will tie everything together.

Pretty In Pink

When in doubt, let the pink do all the talking. Baby pink is not only a gorgeous color, but it looks good on everyone and will catch your new lover’s eye.

Try a pair of vintage denim jeans and pair them with a tight-fitted white tee tucked in. Slip into some white booties or, you guessed it, sneakers. Then, add a pink blazer over the top to polish things off.

Effortless Elegance

On a casual date, stepping things up a notch certainly can’t hurt. Adding a bit of sophistication to your outfit will speak volumes.

But elegance doesn’t always mean you need to try too hard—it’s all the better when it seems like you didn’t even have to try at all. Skip the diamonds but toss on a dressy blouse and match it with a cute, solid mini skirt or some light denim jeans.

Add some spice with a pair of block heels and a classy watch. And don’t forget your favorite bag to tie in the look.

Satin Sweetheart

For a dinner date or an evening meet-up for drinks, a super easy but perfectly pretty choice is a solid satin slip dress.

You don’t need much more to step the ensemble up; the dress puts in enough work. Try it with some simple pumps and a handbag. For more of a casual look, test out a satin midi skirt paired with a loose tee.

Tie your tee up at the waist and lace-up some white sneakers. If you’re in for a colder evening, add a denim jacket to the mix.

Dangerous Dreamer

You didn’t think we’d forget about our leather-lovers, did you? If you’re hoping to give off some baddie vibes, adding a leather jacket to nearly any outfit will easily step your look up a notch—maybe even two.

Wear some dark skinny jeans with your favorite top, and layer your leather jacket on top. Add a pair of edgy shoes to pop in some color.

If you’re hoping to exude sexier bombshell energy, try a mini skirt and a cute blouse, paired with some thigh-high boots and your leather jacket. Not only will you look fierce, but you’ll feel it, too.

Bottom Line

If you’re on the fence about your date-night ensemble, try not to stress; we’ve got your back.

Peer into your closet and see if any of these options will work for you. But, regardless of what you choose to wear on your first date, make sure to slip into something that makes you feel confident and beautiful—being comfortable is key to making a great impression and having a good time.